Field of the Invention
The present invention relates to the field of asymmetric catalysis. More particularly, the invention relates to the field of organometallic catalysts useful for enantioselectively epoxidizing prochiral olefins with a new class of organorhenium complexes (i.e., an optically active metal ligand complex catalyst) as novel catalysts.
Asymmetric epoxidation of an olefin constitutes an extremely appealing strategy for the synthesis of optically active organic compounds. Several advances in this area have occurred in recent years. The most commonly and successfully used catalysts for asymmetric epoxidation of unfunctionalized olefins are porphyrin and salen based systems. Chiral metal porphyrins have been reported to catalyze asymmetric epoxidation of styrene derivatives with high turnover numbers and moderate enantioselectivities (J. P. Collman et al. Science, 1993, 26, 1404). Unfortunately, the chiral porphyrin systems are usually difficult to prepare and are limited to styrene derivatives as substrates. E. N. Jacobsen (J. Am. Chem. Soc. 1990, 112, 2801) and T. Katsuki (Tetrahedron Lett. 1990, 31, 7345) independently reported asymmetric epoxidation of olefins by bleach or iodosobenzene catalyzed by chiral manganese salen complexes. These chiral salen complexes were designed based on Kochi's achiral cationic manganese salen complex that was reported in 1986 (J. Am. Chem. Soc. 1986, 108, 2309). The salen based catalyst gave very high enantioselectivities for the epoxidation of cis olefins, e.g., cis-.beta.-methylstyrene and dihydronaphthalene. However, the turnover numbers of these catalysts are typically 10 to 30, and they are limited to conjugated cis olefins. In 1980, Katsuki and Sharpless (references 43 and 44 below) reported a method for the epoxidation of allylic alcohols which proceeds with high enantioselectivities. However, this method is restricted to only allylic alcohols.
While Herrmann et al. (U.S. Pat. No. 5,155,247) have suggested the use of certain organorhenium compounds as catalysts for the oxidation of multiple C-C bonds, these do not produce a chiral epoxide.
Given the broad synthetic utility of chiral epoxides, more efficient catalytic and enantioselective catalysts besides porphyrin, salen and simple rhenium systems for asymmetric epoxidation of unfunctionalized olefins are clearly desirable.
Description of the Prior Art
The following prior art references are disclosed for informational purposes.
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